Summary
- Sean Connery's love/hate relationship with the James Bond role led him to quit the franchise twice, as he grew tired of the fame, pressure, and being typecast.
- Despite leaving after the fifth film, Connery returned to play Bond in Diamonds Are Forever after George Lazenby's departure, using his salary to establish the Scottish International Education Trust.
- Connery turned down another return in Live and Let Die, stating that after playing 007 six times, his "obligation to play James Bond" had to end, giving his approval to Roger Moore as the perfect Bond. However, he did make one final return in the non-canon Never Say Never Again in 1983.
Sean Connery received high acclaim for his work in the all the actors who have played James Bond.
There are seven James Bond movies starring Sean Connery, six of which were official franchise installments made by EON Productions. He first left the series after five movies and decided he was done with the 007 role. After the sixth James Bond movie flopped, Connery changed his mind and agreed to come back for Diamonds Are Forever. He then hung up his tuxedo again before returning a decade later for a non-EON movie as James Bond.

Every James Bond Movie Ranked From Worst to Best (Including No Time to Die)
With the release of No Time to Die, it's time to rank the James Bond films from worst to best, from Goldfinger to Skyfall, Thunderball to Spectre.
Sean Connery Grew Tired Of Playing 007 After You Only Live Twice
By the time the James Bond franchise had reached its fifth movie, You Only Live Twice, Sean Connery had become bored with his famous role. The actor had become synonymous with James Bond by this point, and he was worried about being typecast in future films. Connery was also fed up with the fame and pressure that came with playing such an iconic character. During the filming of You Only Live Twice, he was hassled by photographers and pursued by unrelenting fans, which only angered him further.
Connery also didn't have a good relationship with the James Bond franchise's producers and was not happy with his salary of $750,000 plus 25 percent of merchandising for the fifth film. He made it known to EON Productions, the company in charge of the franchise, that he wanted a $1 million salary for the sixth movie. When his request was refused, Connery decided he was done with the James Bond role, and he was replaced by George Lazenby for 1969's On Her Majesty's Secret Service.
Why Sean Connery Didn’t Return For Live And Let Die
After the critical and commercial failure of On Her Majesty's Secret Service, it was clear that the James Bond franchise was in trouble. George Lazenby left the role after his sole appearance as lead of the franchise, and recasting Bond was up in the air. Producers decided to ask Sean Connery to return for the next film, offering him a salary of $1.25 million to re-star in the franchise. Totally won over by this offer, Sean Connery agreed to return as James Bond in 1971's Diamonds Are Forever. He used his salary from the film to establish the Scottish International Education Trust.
Diamonds Are Forever proved to be a turning point for the James Bond franchise and gave hope for more movies. But despite being offered a salary of $5.5 million to reprise the role again, Sean Connery turned down Live and Let Die, which instead debuted Roger Moore as James Bond in 1973. Connery made it clear that after playing 007 six times, he’d had enough, telling the screenwriter that his "obligation to play James Bond" had to end at some point.
Connery gave his successor, Roger Moore, his approval and labeled him “the perfect Bond” to carry on the James Bond franchise. Yet one decade later, Connery made one more return to the part of James Bond, this time for an unofficial, non-canon 1983 installment, which competed against Moore's own Bond movie of the same year. That final Connery Bond movie's title, Never Say Never Again, perfectly reflected the actor's tumultuous relationship with the James Bond franchise throughout his career.